Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines was written by McLean, Liam A.;Ashford, Matthew W.;Fyfe, James W. B.;Slawin, Alexandra M. Z.;Leach, Andrew G.;Watson, Allan J. B.. And the article was included in Chemistry – A European Journal in 2022.Reference of 1632-83-3 This article mentions the following:
A method for the synthesis of chiral vicinal chloroamines RCH(Cl)CH2NHR1 [R = 2-quinolyl, quinazolin-2-yl, 1,3-benzothiazol-2-yl, etc.; R1 = Ph, 4-MeC6H4, benzothiophen-5-yl, etc.] via asym. protonation of catalytically generated prochiral chloroenamines using chiral Bronsted acids was reported. The process was highly enantioselective, with the origin of asymmetry and catalyst substituent effects elucidated by DFT calculations The utility of the method showed as an approach to the synthesis of a broad range of heterocycle-substituted aziridines I [R2 = 2-quinolyl, quinoxalin-2-yl, 5-cyano-2-pyridyl, etc.; Ar = Ph, 4-MeOC6H4, 3-BrC6H4, etc.] by treatment of the chloroamines with base in a one-pot process, as well as the utility of the process to allow access to vicinal diamines II [R3 = 4-tert-butoxycarbonylpiperazin-1-yl, morpholino, thiomorpholino]. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Reference of 1632-83-3).
1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Reference of 1632-83-3
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem